LOGIN TO YOUR ACCOUNT

Username
Password
Remember Me
Or use your Academic/Social account:

CREATE AN ACCOUNT

Or use your Academic/Social account:

Congratulations!

You have just completed your registration at OpenAire.

Before you can login to the site, you will need to activate your account. An e-mail will be sent to you with the proper instructions.

Important!

Please note that this site is currently undergoing Beta testing.
Any new content you create is not guaranteed to be present to the final version of the site upon release.

Thank you for your patience,
OpenAire Dev Team.

Close This Message

CREATE AN ACCOUNT

Name:
Username:
Password:
Verify Password:
E-mail:
Verify E-mail:
*All Fields Are Required.
Please Verify You Are Human:
fbtwitterlinkedinvimeoflicker grey 14rssslideshare1
Suberu, John O.; Gorka, Alexander P.; Jacobs, Lauren; Roepe, Paul D.; Sullivan, Neil; Barker, Guy C.; Lapkin, Alexei A. (2013)
Publisher: Public Library of Science
Journal: PLoS ONE
Languages: English
Types: Article
Subjects: RS, Q, R, Research Article, Science, Medicine, RM

Classified by OpenAIRE into

mesheuropmc: parasitic diseases
Artemisia annua hot water infusion (tea) has been used in in vitro experiments against P. falciparum malaria parasites to test potency relative to equivalent pure artemisinin. High performance liquid chromatography (HPLC) and mass spectrometric analyses were employed to determine the metabolite profile of tea including the concentrations of artemisinin (47.5±0.8 mg L(-1)), dihydroartemisinic acid (70.0±0.3 mg L(-1)), arteannuin B (1.3±0.0 mg L(-1)), isovitexin (105.0±7.2 mg L(-1)) and a range of polyphenolic acids. The tea extract, purified compounds from the extract, and the combination of artemisinin with the purified compounds were tested against chloroquine sensitive and chloroquine resistant strains of P. falciparum using the DNA-intercalative SYBR Green I assay. The results of these in vitro tests and of isobologram analyses of combination effects showed mild to strong antagonistic interactions between artemisinin and the compounds (9-epi-artemisinin and artemisitene) extracted from A. annua with significant (IC50 <1 μM) anti-plasmodial activities for the combination range evaluated. Mono-caffeoylquinic acids, tri-caffeoylquinic acid, artemisinic acid and arteannuin B showed additive interaction while rosmarinic acid showed synergistic interaction with artemisinin in the chloroquine sensitive strain at a combination ratio of 1:3 (artemisinin to purified compound). In the chloroquine resistant parasite, using the same ratio, these compounds strongly antagonised artemisinin anti-plasmodial activity with the exception of arteannuin B, which was synergistic. This result would suggest a mechanism targeting parasite resistance defenses for arteannuin B's potentiation of artemisinin.
  • The results below are discovered through our pilot algorithms. Let us know how we are doing!

    • 1. Hsu E (2006) The history of qing hao in the Chinese materia medica. Trans R Soc Trop Med Hyg 100: 505-508. doi:10.1016/j.trstmh. 2005.09.020. PubMed: 16566952.
    • 2. Wright CW, Linley PA, Brun R, Wittlin S, Hsu E (2010) Ancient Chinese methods are remarkably effective for the preparation of artemisinin-rich extracts of Qing Hao with potent antimalarial activity. Molecules 15: 804-812. doi:10.3390/molecules15020804. PubMed: 20335947.
    • 3. O'Neill PM, Barton VE, Ward SA (2010) The molecular mechanism of action of artemisinin-the debate continues. Molecules 15: 1705-1721. doi:10.3390/molecules15031705. PubMed: 20336009.
    • 4. Ding XC, Beck H-P, Raso G (2011) Plasmodium sensitivity to artemisinins: magic bullets hit elusive targets. Trends Parasitol 27: 73-81. doi:10.1016/j.pt.2010.11.006. PubMed: 21169061.
    • 5. Pandey AV, Tekwani BL, Singh RL, Chauhan VS (1999) Artemisinin, an endoperoxide antimalarial, disrupts the hemoglobin catabolism and heme detoxification systems in malarial parasite. J Biol Chem 274: 19383-19388. doi:10.1074/jbc.274.27.19383. PubMed: 10383451.
    • 6. Jefford CW (2001) Why artemisinin and certain synthetic peroxides are potent antimalarials. Implications for the mode of action. Curr Med Chem 8: 1803-1826. doi:10.2174/0929867013371608. PubMed: 11772352.
    • 7. Eckstein-Ludwig U, Webb RJ, Van Goethem ID, East JM, Lee AG et al. (2003) Artemisinins target the SERCA of Plasmodium falciparum. Nature 424: 957-961. doi:10.1038/nature01813. PubMed: 12931192.
    • 8. Wang J, Huang L, Li J, Fan Q, Long Y et al. (2010) Artemisinin Directly Targets Malarial Mitochondria through Its Specific Mitochondrial Activation. PLOS ONE 5: e9582. doi:10.1371/journal.pone.0009582. PubMed: 20221395.
    • 9. Li W, Mo W, Shen D, Sun L, Wang J et al. (2005) Yeast Model Uncovers Dual Roles of Mitochondria in the Action of Artemisinin. PLOS Genet 1: e36. doi:10.1371/journal.pgen.0010036. PubMed: 16170412.
    • 10. Haynes RK, Monti D, Taramelli D, Basilico N, Parapini S et al. (2003) Artemisinin antimalarials do not inhibit hemozoin formation. Antimicrob Agents Chemother 47: 1175-1175. doi:10.1128/AAC.47.3.1175.2003. PubMed: 12604568.
    • 11. Golenser J, Waknine JH, Krugliak M, Hunt NH, Grau GE (2006) Current perspectives on the mechanism of action of artemisinins. Int J Parasitol 36: 1427-1441. doi:10.1016/j.ijpara.2006.07.011. PubMed: 17005183.
    • 12. Eastman RT, Fidock DA (2009) Artemisinin-based combination therapies: a vital tool in efforts to eliminate malaria. Nat Rev Microbiol 7: 864-874. PubMed: 19881520.
    • 13. Klonis N, Crespo-Ortiz MP, Bottova I, Abu-Bakar N, Kenny S et al. (2011) Artemisinin activity against Plasmodium falciparum requires hemoglobin uptake and digestion. Proc Natl Acad Sci USA 108: 11405-11410. doi:10.1073/pnas.1104063108. PubMed: 21709259.
    • 14. Haynes RK (2006) From artemisinin to new artemisinin antimalarials: biosynthesis, extraction, old and new derivatives, stereochemistry and medicinal chemistry requirements. Curr Top Med Chem 6: 509-537. doi:10.2174/156802606776743129. PubMed: 16719805.
    • 15. Weina PJ (2008) Artemisinins from Folklore to Modern MedicineTransforming an Herbal Extract to Life-Saving Drugs. Parassitologia 50: 25-29. PubMed: 18693553.
    • 16. Jansen FH (2006) The herbal tea approach for artemisinin as a therapy for malaria? Trans R Soc Trop Med Hyg 100: 285-286. doi:10.1016/ j.trstmh.2005.08.004. PubMed: 16274712.
    • 17. WHO Report (2012) WHO position statement on effectiveness of nonpharmaceutical forms of Artemisia annua L. against malaria. Available: http://www.who.int/malaria/ position_statement_herbal_remedy_artemisia_annua_l.pdf.
    • 18. Hsu E (2006) Reflections on the discovery of the antimalarial qinghao. Br J Clin Pharmacol 61: 666-670. doi:10.1111/j. 1365-2125.2006.02673.x. PubMed: 16722826.
    • 19. Rath K, Taxis K, Walz G, Gleiter CH, Li SM et al. (2004) Pharmacokinetic study of artemisinin after oral intake of a traditional preparation of Artemisia annua L.(annual wormwood). The American journal of tropical medicine and hygiene 70: 128-132.
    • 20. De Ridder S, Van der Kooy F, Verpoorte R (2008) Artemisia annua as a self-reliant treatment for malaria in developing countries. J Ethnopharmacol 120: 302-314. doi:10.1016/j.jep.2008.09.017. PubMed: 18977424.
    • 21. Van der Kooy F, Verpoorte R (2011) The Content of Artemisinin in the Artemisia annua Tea Infusion. Planta Medica-Natural Products and Medicinal. J Plant Res 77: 1754. doi:10.1055/s-0030-1271065.
    • 22. Mouton J, Jansen O, Frédérich M, van der Kooy F (2013) Is Artemisinin the Only Antiplasmodial Compound in the Artemisia annua Tea Infusion? An in Vitro Study. Planta Med 79: 468-470. doi:10.1055/ s-0032-1328324. PubMed: 23512495.
    • 23. Willcox M, Bodeker G, Bourdy G, Dhingra V, Falquet J et al. (2004) Artemisia annua as a traditional herbal antimalarial. Tradit Med Plants Malar: 43-59.
    • 24. Liu K, Yang S-L, Roberts M, Elford B, Phillipson J (1992) Antimalarial activity of Artemisia annua flavonoids from whole plants and cell cultures. Plant Cell Rep 11: 637-640.
    • 25. Elford BC, Roberts MF, Phillipson JD, Wilson RJM (1987) Potentiation of the antimalarial activity of qinghaosu by methoxylated flavones. Trans R Soc Trop Med Hyg 81: 434-436. doi: 10.1016/0035-9203(87)90161-1. PubMed: 3318019.
    • 26. Bilia AR, Lazari D, Messori L, Taglioli V, Temperini C et al. (2002) Simple and rapid physico-chemical methods to examine action of antimalarial drugs with hemin: its application to Artemisia annua constituents. Life Sci 70: 769-778. doi:10.1016/ S0024-3205(01)01447-3. PubMed: 11833740.
    • 27. Weathers PJ, Towler MJ (2012) The flavonoids casticin and artemetin are poorly extracted and are unstable in an Artemisia annua tea infusion. Planta Med 78: 1024-1026. doi:10.1055/s-0032-1314949. PubMed: 22673829.
    • 28. Carbonara T, Pascale R, Argentieri MP, Papadia P, Fanizzi FP et al. (2012) Phytochemical analysis of a herbal tea from Artemisia annua L. J Pharm Biomed Anal 62: 79-86. doi:10.1016/j.jpba.2012.01.015. PubMed: 22305080.
    • 29. Zhang B, Yang R, Liu CZ (2008) Microwave-assisted extraction of chlorogenic acid from flower buds of Lonicera japonica Thunb. Sep Purif Technol 62: 480-483. doi:10.1016/j.seppur.2008.02.013.
    • 30. Feng R, Lu Y, Bowman LL, Qian Y, Castranova V et al. (2005) Inhibition of activator protein-1, NF-kappaB, and MAPKs and induction of phase 2 detoxifying enzyme activity by chlorogenic acid. J Biol Chem 280: 27888-27895. doi:10.1074/jbc.M503347200. PubMed: 15944151.
    • 31. Miketova P, Schram KH, Whitney J, Kearns EH, Timmermann BN (1999) Mass spectrometry of 3,5- and 4,5-dicaffeoylquinic acids and selected derivatives. J Mass Spectrom 34: 1240-1252. doi:10.1002/ (SICI)1096-9888(199912)34:12. PubMed: 10587617.
    • 32. Belkaid A, Currie J-C, Desgagnés J, Annabi B (2006) The chemopreventive properties of chlorogenic acid reveal a potential new role for the microsomal glucose-6-phosphate translocase in brain tumor progression. Cancer Cell Int 6: 7. doi:10.1186/1475-2867-6-7. PubMed: 16566826.
    • 33. De Donno A, Grassi T, Idolo A, Guido M, Papadia P et al. (2012) Firsttime comparison of the in vitro antimalarial activity of Artemisia annua herbal tea and artemisinin. Trans R Soc Trop Med Hyg 106: 696-700. doi:10.1016/j.trstmh.2012.07.008. PubMed: 22986092.
    • 34. Wang L-H, Song Y-T, Chen Y, Cheng Y-Y (2007) Solubility of Artemisinin in Ethanol + Water from (278.2 to 343.2) K. J Chem Eng Data 52: 757-758. doi:10.1021/je0603426.
    • 35. Suberu J, Song L, Slade S, Sullivan N, Barker G et al. (2013) A rapid method for the determination of artemisinin and its biosynthetic precursors in Artemisia annua L. crude extracts. J Pharm Biomed Anal 84: 269-277. doi:10.1016/j.jpba.2013.06.025. PubMed: 23867088.
    • 36. Bennett TN, Paguio M, Gligorijevic B, Seudieu C, Kosar AD et al. (2004) Novel, rapid, and inexpensive cell-based quantification of antimalarial drug efficacy. Antimicrob Agents Chemother 48: 1807-1810. doi:10.1128/AAC.48.5.1807-1810.2004. PubMed: 15105139.
    • 37. Bray PG, Deed S, Fox E, Kalkanidis M, Mungthin M et al. (2005) Primaquine synergises the activity of chloroquine against chloroquineresistant P. falciparum. Biochem Pharmacol 70: 1158-1166. doi: 10.1016/j.bcp.2005.07.021. PubMed: 16139253.
    • 38. Berenbaum MC (1978) A method for testing for synergy with any number of agents. J Infect Dis 137: 122-130. doi:10.1093/infdis/ 137.2.122. PubMed: 627734.
    • 39. Vivas L, Rattray L, Stewart LB, Robinson BL, Fugmann B et al. (2007) Antimalarial efficacy and drug interactions of the novel semi-synthetic endoperoxide artemisone in vitro and in vivo. J Antimicrob Chemother 59: 658-665. doi:10.1093/jac/dkl563. PubMed: 17337512.
    • 40. Fivelman QL, Adagu IS, Warhurst DC (2004) Modified fixed-ratio isobologram method for studying in vitro interactions between atovaquone and proguanil or dihydroartemisinin against drug-resistant strains of Plasmodium falciparum. Antimicrob Agents Chemother 48: 4097-4102. doi:10.1128/AAC.48.11.4097-4102.2004. PubMed: 15504827.
    • 41. Friedman M (1997) Chemistry, biochemistry, and dietary role of potato polyphenols. A review. J Agric Food Chem 45: 1523-1540. doi:10.1021/ jf960900s.
    • 42. Noratto G, Porter W, Byrne D, Cisneros-Zevallos L (2009) Identifying peach and plum polyphenols with chemopreventive potential against estrogen-independent breast cancer cells. J Agric Food Chem 57: 5219-5226. doi:10.1021/jf900259m. PubMed: 19530711.
    • 43. De Magalhaes PM, Dupont I, Hendrickx A, Joly A, Raas T et al. (2012) Anti-inflammatory effect and modulation of cytochrome P450 activities by Artemisia annua tea infusions in human intestinal Caco-2 cells. Food Chem 134: 864-871. doi:10.1016/j.foodchem.2012.02.195. PubMed: 23107701.
    • 44. Willcox M (2009) Artemisia species: from traditional medicines to modern antimalarials-and back again. J Altern Complement Med 15: 101-109. doi:10.1089/acm.2008.0327. PubMed: 19236169.
    • 45. Acton N, Klayman DL (1987) Conversion of artemisinin (qinghaosu) to iso-artemisitene and to 9-epi-artemisinin1. Planta Med 53: 266-268. doi:10.1055/s-2006-962700. PubMed: 17269016.
    • 46. Woerdenbag HJ, Moskal TA, Pras N, Malingré TM, El-Feraly FS et al. (1993) Cytotoxicity of Artemisinin-Related Endoperoxides to Ehrlich Ascites Tumor Cells. J Nat Prod 56: 849-856. doi:10.1021/ np50096a007. PubMed: 8350087.
    • 47. Wagner H, Ulrich-Merzenich G (2009) Synergy research: Approaching a new generation of phytopharmaceuticals. Phytomedicine 16: 97-110. doi:10.1016/j.phymed.2008.12.018. PubMed: 19211237.
    • 48. Wagner H (2011) Synergy research: Approaching a new generation of phytopharmaceuticals. Fitoterapia 82: 34-37. doi:10.1016/j.fitote. 2010.11.016. PubMed: 21075177.
    • 49. Wagner H (2005) Natural products chemistry and phytomedicine in the 21st century: new developments and challenges. Pure Appl Chem 77: 1-6. doi:10.1351/pac200577010001.
    • 50. Yordi EG, Pérez EM, Matos MJ, Villares EU (2012) Antioxidant and Pro-Oxidant Effects of Polyphenolic Compounds and Structure-Activity Relationship Evidence. Nutrition, Well-Being and Health. Intech.
    • 51. Nemeikaitė-Čėnienė A, Imbrasaite A, Sergediene E, Čėnas N (2005) Quantitative structure-activity relationships in prooxidant cytotoxicity of polyphenols: role of potential of phenoxyl radical/phenol redox couple. Arch Biochem Biophys 441: 182-190. doi:10.1016/j.abb.2005.07.002. PubMed: 16111645.
    • 52. Cui L, Wang ZL, Miao J, Miao M, Chandra R et al. (2012) Mechanisms of in vitro resistance to dihydroartemisinin in Plasmodium falciparum. Mol Microbiol 86: 111-128. doi:10.1111/j.1365-2958.2012.08180.x. PubMed: 22812578.
    • 53. Sidhu ABS, Uhlemann A-C, Valderramos SG, Valderramos J-C, Krishna S et al. (2006) Decreasing pfmdr1 copy number in Plasmodium falciparum malaria heightens susceptibility to mefloquine, lumefantrine, halofantrine, quinine, and artemisinin. J Infect Dis 194: 528-535. doi: 10.1086/507115. PubMed: 16845638.
    • 54. Erkan N, Ayranci G, Ayranci E (2008) Antioxidant activities of rosemary (Rosmarinus Officinalis L.) extract, blackseed (Nigella sativa L.) essential oil, carnosic acid, rosmarinic acid and sesamol. Food Chemistry 110: 76-82.
    • 55. Petersen M, Simmonds MSJ (2003) Rosmarinic acid. Phytochemistry 62: 121-125. doi:10.1016/S0031-9422(02)00513-7. PubMed: 12482446.
    • 56. Tepe B, Eminagaoglu O, Akpulat HA, Aydin E (2007) Antioxidant potentials and rosmarinic acid levels of the methanolic extracts of Salvia verticillata (L.) subsp. verticillata and S. verticillata (L.) subsp. amasiaca (Freyn & Bornm.) Bornm. Food Chemistry 100: 985-989..
    • 57. Gülçin İ (2006) Antioxidant activity of caffeic acid (3,4- dihydroxycinnamic acid). Toxicology 217: 213-220. doi:10.1016/j.tox. 2005.09.011. PubMed: 16243424.
    • 58. Xu J-G, Hu Q-P, Liu Y (2012) Antioxidant and DNA-Protective Activities of Chlorogenic Acid Isomers. J Agric Food Chem 60: 11625-11630. doi: 10.1021/jf303771s. PubMed: 23134416.
    • 59. Cao D, Li H, Yi J, Zhang J, Che H et al. (2011) Antioxidant Properties of the Mung Bean Flavonoids on Alleviating Heat Stress. PLOS ONE 6: e21071. doi:10.1371/journal.pone.0021071. PubMed: 21695166.
    • 60. Bozdech Z, Ginsburg H (2004) Antioxidant defense in Plasmodium falciparum-data mining of the transcriptome. Malar J 3: 23. doi: 10.1186/1475-2875-3-23. PubMed: 15245577.
    • 61. Agrawal PK, Vishwakarma RA, Jain DC, Roy R (1991) High field NMR spectroscopic studies of arteannuin B and a reappraisal of the structure of arteannuin C. Phytochemistry 30: 3469-3471. doi: 10.1016/0031-9422(91)83234-C.
    • 62. Lansbury PT, Mojica CA (1986) Total synthesis of (±)-arteannuin B. Tetrahedron Lett 27: 3967-3970. doi:10.1016/S0040-4039(00)84886-8.
  • No related research data.
  • Discovered through pilot similarity algorithms. Send us your feedback.

Share - Bookmark

Cite this article